Water → HCID 67328339, compound

Participants

Reaction Steps

To stirred solution containing 502 mg (1.15 mmol) of 5-(benzyloxy)-4-decyl-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidine in 10 mL of ethanol-water 9:1 were added 800 mg (11.50 mmol) of hydroxylamine hydrochloride. The reaction mixture was then stirred at reflux during 5 h. A second portion of 800 mg (11.50 mmol) of hydroxylamine hydrochloride was added and the reaction mixture was stirred at reflux for 16 h. The reaction mixture was then poured into 70 mL of water and then basified to a pH 9-10 with a 1N NaOH aqueous solution. The mixture was extracted with two 70-mL portions of ethyl acetate. The combined organic layer was washed with a 70-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×3 cm). Elution with 3:2 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 305 mg (75%); silica gel TLC Rf 0.25 (3:2 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.85 (t, 3H, J=6.4 Hz), 1.26 (m, 14H), 1.61 (m, 2H), 2.27 (s, 3H), 2.56 (dd, 2H, J=8.0, 8.0 Hz), 4.71 (s, 2H), 5.24 (br s, 2H) and 7.35-7.40 (m, 5H); 13C NMR (CDCl3) δ 13.94, 18.86, 22.64, 28.41, 29.27, 29.39, 29.50, 29.55, 29.71, 31.87, 31.88, 75.88, 127, 88, 128.24, 128.24, 128.58, 128.58, 136.79, 142.8, 158.92, 161.09 and 162.82; mass spectrum (APCI), m/z 356.2704 (M+H)+ (C22H34N3O requires 356.2702).

Provenance & Evidence